| Identification | Back Directory | [Name]
6-Fluoroquinoline | [CAS]
396-30-5 | [Synonyms]
6-Fluoroquinolin
6-Fluoroquinoine
6-Fluoroquinoline
6-Fluoroquinoline>
Quinoline, 6-fluoro- | [Molecular Formula]
C9H6FN | [MDL Number]
MFCD01685512 | [MOL File]
396-30-5.mol | [Molecular Weight]
147.15 |
| Chemical Properties | Back Directory | [Boiling point ]
126°C/30mmHg(lit.) | [density ]
1.209 g/mL at 25 °C | [refractive index ]
n20/D1.592 | [RTECS ]
VB8370020 | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Oil | [pka]
4.32±0.10(Predicted) | [color ]
Clear Colorless | [λmax]
330nm(EtOH)(lit.) | [InChI]
1S/C9H6FN/c10-8-3-4-9-7(6-8)2-1-5-11-9/h1-6H | [InChIKey]
RMDCSDVIVXJELQ-UHFFFAOYSA-N | [SMILES]
Fc1ccc2ncccc2c1 |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22-41 | [Safety Statements ]
26-39 | [WGK Germany ]
3 | [HS Code ]
2933491090 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1 |
| Hazard Information | Back Directory | [Uses]
6-Fluoroquinoline, is a versatile building block used in the synthesis of various chemical compounds. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 56, p. 7288, 1991 DOI: 10.1021/jo00026a019 | [Synthesis]
General procedure for the synthesis of 6-fluoroquinoline from 6-fluoro-1,2,3,4-tetrahydroquinoline: To a 10 mL round-bottomed flask fitted with a magnetic stirring bar, 6-fluoro-1,2,3,4-tetrahydroquinoline (0.5 mmol), 40 wt% toluene solution (2.2 equiv., 1.1 mmol, 0.5 mL), and a DEAD solution of CHCl3 ( 1.0 mL). The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the mixture was concentrated using a rotary evaporator. The residue was purified by column chromatography using EtOAc: hexane (1:5) as eluent to give 6-fluoroquinoline. For compounds 2f and 2m, the product spot was close to the spot of residual DEAD. To remove residual DEAD, 1 equivalent of PPh3 was added after the reaction and the reaction mixture was stirred for 10 min. Subsequently, the reaction mixture was concentrated using a rotary evaporator. The residue was purified by column chromatography using CHCl3: hexane (1:1) as eluent to give the final 6-fluoroquinoline. | [References]
[1] Organic Letters, 2015, vol. 17, # 18, p. 4404 - 4407
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 11, p. 3080 - 3084
[3] Angew. Chem., 2017, vol. 129, # 11, p. 3126 - 3130,5
[4] Organic Letters, 2016, vol. 18, # 24, p. 6300 - 6303
[5] Synthetic Communications, 2018, vol. 48, # 11, p. 1291 - 1298 |
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